Two new series of sixteen compounds of thiosemicarbazide and 1,3,4-thiadiazole derivatives containing benzofuran and pyrazole moieties were synthesised in order to study the effect of such combinations on the expected antimicrobial activity. In first series synthesis of eight novel 1-(5-(5-H/Br benzofuran-2-yl)-1-phenyl-1H-pyrazole-3- carbonyl)-4-substituted/ unsubstituted phenyl thiosemicarbazides (3a-h) have been achieved through an interaction of 5(5-H/Br benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazides(1a-b) with different arylisothiocyanates (2a-h). Second series comprise of eight novel derivatives of 5-(5-(5-H/Br benzofuran-2-yl)-1-phenyl-1H-pyrazol-3- yl)-N-substituted / unsubstituted phenyl-1,3,4-thiadiazol-2-amine (4a-h) have also been synthesised by cyclodehydration of (3a-h) with cold concentrated sulfuric acid. The structures of the newly synthesized compounds were assigned on the basis of elemental analysis and spectral studies like IR, 1H NMR and Mass spectra. The novel synthesized title compounds were screened for their in-vitro antimicrobial activity at different concentrations and have shown their potent activity against tested bacterial strain.